Azine-based charge transport materials having a bicyclic heterocyclic ring

Abstract

Improved organophotoreceptor comprises an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising: (a) a charge transport material having the formula where Y comprises an aromatic group; X is a —(CH 2 ) n — group, where n is an integer between 1 and 10, inclusive, and one or more of the methylene groups is optionally replaced by another atom or group; Q 1 , Q 2 , and Q 3 are, each independently, O, S, or NR; and R, R 1 , R 2 , and R 3 comprise, each independently, H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an alkylsulfanyl group, an aromatic group, or a heterocyclic group; and (b) a charge generating compound. Corresponding electrophotographic apparatuses and imaging methods are described.

1. An organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising:
 (a) a charge transport material having the formula 
 
       
         
           
           
               
               
           
         
         where Y comprises an aromatic group; 
         X is a —(CH 2 ) n — group, where n is an integer between 1 and 10, inclusive, and one or more of the methylene groups is optionally replaced by O, S, C═O, O═S═O, an NR a  group, or a CR c R d  group, where R a , R c , and R d , are, each independently, H, a hydroxyl group, a thiol group, a carboxyl group, an amino group, a halogen, an alkyl group, an acyl group, or an alkoxy group; 
         Q 1 , Q 2 , and Q 3  are, each independently, O, S, or NR; 
         R 1  comprises H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group; 
         R and R 2  comprise, each independently, H, an alkyl group, or an alkoxy group; and 
         R 3  comprises a bond linking Y and the carbon atom adjacent to Y, H, an alkyl group, or an alkoxy group; and 
         (b) a charge generating compound. 
       
     
     
       2. An organophotoreceptor according to  claim 1  wherein R 1 , R 2 , and R 3  are each H; and Q 2  and Q 3  are each O. 
     
     
       3. An organophotoreceptor according to  claim 1  wherein Y comprises an arylamine group. 
     
     
       4. An organophotoreceptor according to  claim 3  wherein the arylamine group is selected from the group consisting of an (N,N-disubstituted)arylamine group, a carbazolyl group, and a julolidinyl group. 
     
     
       5. An organophotoreceptor according to  claim 1  wherein Y is a fluorenylidenyl group and R 3  is a bond between Y and the carbon atom adjacent to Y. 
     
     
       6. An organophotoreceptor according to  claim 5  wherein X is a —(CH 2 ) n — group where n is an integer between 1 and 3. 
     
     
       7. An organophotoreceptor according to  claim 1  wherein R 1  comprises an aromatic group selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
         where Z 1  and Z 2 , each independently, comprise H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group. 
       
     
     
       8. An organophotoreceptor according to  claim 7  wherein Z 1  and Z 2 , each independently, are selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
       
     
     
       9. An organophotoreceptor according to  claim 1  wherein the photoconductive element further comprises a second charge transport material. 
     
     
       10. An organophotoreceptor according to  claim 9  wherein the second charge transport material comprises an electron transport compound. 
     
     
       11. An organophotoreceptor according to  claim 1  wherein the photoconductive element further comprises a binder. 
     
     
       12. An electrophotographic imaging apparatus comprising:
 (a) a light imaging component; and 
 (b) an organophotoreceptor oriented to receive light from the light imaging component, the organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising:
 (i) a charge transport material having the formula 
 
 
       
         
           
           
               
               
           
         
         where Y comprises an aromatic group; 
         X is a —(CH 2 ) n — group, where n is an integer between 1 and 10, inclusive, and one or more of the methylene groups is optionally replaced by O, S, C═O, O═S═O, an NR a  group, or a CR c R d  group, where R a , R c , and R d , are, each independently, H, a hydroxyl group, a thiol group, a carboxyl group, an amino group, a halogen, an alkyl group, an acyl group, or an alkoxy group; 
         Q 1 , Q 2 , and Q 3  are, each independently, O, S, or NR; 
         R 1  comprises H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group; 
         R and R 2  comprise, each independently, H, an alkyl group, or an alkoxy group; and 
         R 3  comprises a bond linking Y and the carbon atom adjacent to Y, H, an alkyl group, or an alkoxy group; and
 (ii) a charge generating compound. 
 
       
     
     
       13. An electrophotographic imaging apparatus according to  claim 12  wherein R 1 , R 2 , and R 3  are each H; and Q 2  and Q 3  are each O. 
     
     
       14. An electrophotographic imaging apparatus according to  claim 12  wherein Y comprises an arylamine group. 
     
     
       15. An electrophotographic imaging apparatus according to  claim 14  wherein the arylamine group is selected from the group consisting of an (N,N-disubstituted)arylamine group, a carbazolyl group, and a julolidinyl group. 
     
     
       16. An electrophotographic imaging apparatus according to  claim 12  wherein Y is a fluorenylidenyl group and R 3  is a bond between Y and the carbon atom adjacent to Y. 
     
     
       17. An electrophotographic imaging apparatus according to  claim 16  wherein X is a —(CH 2 ) n — group where n is an integer between 1 and 3. 
     
     
       18. An electrophotographic imaging apparatus according to  claim 12  wherein R 1  comprises an aromatic group selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
       
       where Z 1  and Z 2 , each independently, comprise H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group. 
     
     
       19. An electrophotographic imaging apparatus according to  claim 18  wherein Z 1  and Z 2 , each independently, are selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
       
     
     
       20. An electrophotographic imaging apparatus according to  claim 12  wherein the photoconductive element further comprises a second charge transport material. 
     
     
       21. An electrophotographic imaging apparatus according to  claim 20  wherein second charge transport material comprises an electron transport compound. 
     
     
       22. An electrophotographic imaging apparatus according to  claim 12  further comprising a toner dispenser. 
     
     
       23. An electrophotographic imaging process comprising;
 (a) applying an electrical charge to a surface of an organophotoreceptor comprising an electrically conductive substrate and a photoconductive element on the electrically conductive substrate, the photoconductive element comprising
 (i) a charge transport material having the formula 
 
 
       
         
           
           
               
               
           
         
         where Y comprises an aromatic group; 
         X is a —(CH 2 ) n — group, where n is an integer between 1 and 10, inclusive, and one or more of the methylene groups is optionally replaced by O, S, C═O, O═S═O, an NR a  group, or a CR c R d  group, where R a , R c , and R d  are, each independently, H, a hydroxyl group, a thiol group, a carboxyl group, an amino group, a halogen, an alkyl group, an acyl group, an alkoxy group; 
         Q 1 , Q 2 , and Q 3  are, each independently, O, S, or NR; 
         R 1  comprises H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group; 
         R and R 2  comprise, each independently, H, an alkyl group, or an alkoxy group; and 
         R 3  comprises a bond linking Y and the carbon atom adjacent to Y, H, an alkyl group, or an alkoxy group; and
 (ii) a charge generating compound, 
 
         (b) imagewise exposing the surface of the organophotoreceptor to radiation to dissipate charge in selected areas and thereby form a pattern of charged and uncharged areas on the surface; 
         (c) contacting the surface with a toner to create a toned image; and 
         (d) transferring the toned image to substrate. 
       
     
     
       24. An electrophotographic imaging process according to  claim 23  wherein R 1 , R 2 , and R 3  are each H; and Q 2  and Q 3  are each O. 
     
     
       25. An electrophotographic imaging process according to  claim 23  wherein Y comprises an arylamine group. 
     
     
       26. An electrophotographic imaging process according to  claim 25  wherein the arylamine group is selected from the group consisting of an (N,N-disubstituted)arylamine group, a carbazolyl group, and a julolidinyl group. 
     
     
       27. An electrophotographic imaging process according to  claim 23  wherein Y is a fluorenylidenyl group and R 3  is a bond between Y and the carbon atom adjacent to Y. 
     
     
       28. An electrophotographic imaging process according to  claim 27  wherein X is a —(CH 2 ) n — group where n is an integer between 1 and 3. 
     
     
       29. An electrophotographic imaging process according to  claim 23  wherein R 1  comprises an aromatic group selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
         where Z 1  and Z 2 , each independently, comprise H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group. 
       
     
     
       30. An electrophotographic imaging process according to  claim 29  wherein Z 1  and Z 2 , each independently, are selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
       
     
     
       31. An electrophotographic imaging process according to  claim 23  wherein the photoconductive element further comprises a second charge transport material. 
     
     
       32. An electrophotographic imaging process according to  claim 31  wherein the second charge transport material comprises an electron transport compound. 
     
     
       33. An electrophotographic imaging process according to  claim 23  wherein the photoconductive element further comprises a binder. 
     
     
       34. An electrophotographic imaging process according to  claim 23  wherein the toner comprises colorant particles. 
     
     
       35. A charge transport material having the formula 
       
         
           
           
               
               
           
         
         where Y comprises an aromatic group; 
         X is a —(CH 2 ) n — group, where n is an integer between 1 and 10, inclusive, and one or more of the methylene groups is optionally replaced by O, S, C═O, O═S═O, an NR a  group, or a CR c R d  group, where R a , R c , and R d  are, each independently, H, a hydroxyl group, a thiol group, a carboxyl group, an amino group, a halogen, an alkyl group, an acyl group, an alkoxy group; 
         Q 1 , Q 2 , and Q 3  are, each independently, O, S, or NR; 
         R 1  comprises H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group; 
         R and R 2  comprise, each independently, H, an alkyl group, or an alkoxy group; and 
         R 3  comprises a bond linking Y and the carbon atom adjacent to Y, H, an alkyl group, or an alkoxy group. 
       
     
     
       36. A charge transport material according to  claim 35  wherein R 1 , R 2 , and R 3  are each H; and Q 2  and Q 3  are each O. 
     
     
       37. A charge transport material according to  claim 35  wherein Y comprises an arylamine group. 
     
     
       38. A charge transport material according to  claim 37  wherein the arylamine group is selected from the group consisting of an (N,N-disubstituted)arylamine group, a carbazolyl group, and a julolidinyl group. 
     
     
       39. A charge transport material according to  claim 35  wherein Y is a fluorenylidenyl group and R 3  is a bond between Y and the carbon atom adjacent to Y. 
     
     
       40. A charge transport material according to  claim 39  wherein X is a —(CH 2 ) n — group where n is an integer between 1 and 3. 
     
     
       41. A charge transport material according to  claim 35  wherein R 1  comprises an aromatic group selected from the group consisting of the following formulae: 
       
         
           
           
               
               
           
         
       
       where Z 1  and Z 2 , each independently, comprise H, an alkyl group, an alkenyl group, an alkynyl group, an amino group, an acyl group, an alkoxy group, an aromatic group, or a heterocyclic group. 
     
     
       42. A charge transport material according to  claim 41  wherein Z 1  and Z 2 , each independently, are selected from the group consisting of the following formulae: